Media

IF YOU’RE NOT ALL IN

— YOU’RE OUT —

SOME MEDIA STUFF

What’s Your Unfair Advantage?

My memory’s a little cloudy, but I’m pretty sure this is exactly how it played out in real life. Cheers to Zach Braff for getting me my SAG card and the DVD screeners that come with it.

Shark Tank4.29.16

Shark Fight Over Brightwheel

Mixing it up with Cuban is nothing short of a sport for me and Daymond’s vintage shanking move shows how much he enjoys his ringside seat. In the end, Brightwheel might be one of Shark’s best deals ever.

Startup Podcast #19.15.14

How Not to Pitch a Billionaire

Who would’ve guessed when I agreed to do a podcast about launching a podcasting startup that it would get turned into a TV show? Only someone with Alex Blumberg’s masterful storytelling skills could have pulled this off.

The Tim Ferriss Show5.30.15

Be Different & Make Billions

Tim and I sat down on Necker Island in the BVI’s to catch up on the startups whales that got away, how not to drown, and a letter to me from my 20-year-old self.

Shark Tank2.17.17

Two Sharks Better Than One?

Lori and I didn’t team up on a lot of investments, but few things bring people together like the chance to yank a deal from Cuban. That it was in such a great company as Toymail makes it all the better.

Bill Simmons4.26.16

Billionaire Investor Chris Sacca

I’m glad this didn’t turn into a quiz about my NBA trivia chops. Bill is one of the most eerily brilliant I know, so this chat goes down among my all-time favorites.

The Tim Ferriss Show1.15.16

Mullet Wigs Change Everything

I didn’t have time to get to a real soundproof studio. So I followed Timmy’s advice and threw a blanket over my head to tape this episode where I chew on questions from Reddit users.

Keen on Learning7.20.10

What Didn’t I Learn at Google?

Wow, the last eight years have blown by. I’m glad to say this was the first and last time I was introduced as a “micro VC.” Funny how the Google observations hold up.

The Deal10.22.08

Early Days of Angel Investing

Who is that child in a blazer? Ten years ago would I have believed that Lowercase would be this big? Yes. But should anyone else have believed me? No.